CN116172944A - Preparation method and application of temperature/pH response ginsenoside-carrying hydrogel - Google Patents

Preparation method and application of temperature/pH response ginsenoside-carrying hydrogel Download PDF

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CN116172944A
CN116172944A CN202310185197.XA CN202310185197A CN116172944A CN 116172944 A CN116172944 A CN 116172944A CN 202310185197 A CN202310185197 A CN 202310185197A CN 116172944 A CN116172944 A CN 116172944A
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ginsenoside
temperature
carboxymethyl chitosan
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李美贤
卢焕俊
莫慧琳
任煜
张伟
张瑜
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Nantong University
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Abstract

The invention relates to the technical field of biological materials, in particular to a preparation method and application of a temperature/pH response ginsenoside-carrying hydrogel, which comprises the following steps: dissolving O-carboxymethyl chitosan in deionized water, mechanically stirring to obtain O-carboxymethyl chitosan water solution, adding proper amount of 4-dimethylaminopyridine and N, N' -dicyclohexylcarbodiimide, uniformly stirring, adding proper amount of ginsenoside Rh2 solution, uniformly stirring, allowing ginsenoside Rh2 to fully react with O-carboxymethyl chitosan, and dialyzing and freeze-drying after the reaction is finished to obtain ginsenoside Rh 2-carrying O-carboxymethyl chitosan; dissolving the obtained O-carboxymethyl chitosan carrying ginsenoside Rh2 in PBS buffer solution, adding proper amount of polyoxyethylene polyoxypropylene ether, and uniformly stirring to obtain the temperature/pH response ginsenoside-carrying hydrogel. The temperature/pH response ginsenoside-carrying hydrogel obtained by the invention has excellent biocompatibility and simultaneously has temperature and pH response properties.

Description

Preparation method and application of temperature/pH response ginsenoside-carrying hydrogel
Technical Field
The invention relates to the technical field of biological materials, in particular to a preparation method and application of a temperature/pH response ginsenoside-carrying hydrogel.
Background
The O-carboxymethyl chitosan is water-soluble chitosan, has good antibacterial and antitumor activities, and can inhibit itch and other functions, so that the O-carboxymethyl chitosan is widely applied in the field of medicines. In addition, ginsenoside as a representative ingredient of ginseng has the effects of resisting oxidation, resisting inflammation, relieving pain and itching, resisting cancer and the like, including abdominal pain, neuralgia, chronic arthralgia and the like, and can treat pain and itching diseases, so that the ginsenoside is paid more attention to more people. In order to prolong the drug effect of ginsenoside, the release rate of the ginsenoside needs to be effectively regulated.
In order to solve the problems, the application provides a preparation method and application of a temperature/pH response ginsenoside-carrying hydrogel.
Disclosure of Invention
The invention aims to solve the defects in the prior art, and provides a preparation method and application of a temperature/pH response ginsenoside-carrying hydrogel, wherein the prepared ginsenoside-carrying hydrogel has good biocompatibility, can effectively control the release rate of ginsenoside Rh2, and can be applied to the field of drug delivery.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
a preparation method of temperature/pH response ginsenoside-carrying hydrogel comprises the following specific steps:
step 1: dissolving O-carboxymethyl chitosan in deionized water, and mechanically stirring to obtain O-carboxymethyl chitosan aqueous solution;
step 2: dissolving ginsenoside Rh2 in methanol, and mechanically stirring to obtain ginsenoside Rh2 solution;
step 3: adding a proper amount of 4-dimethylaminopyridine and N, N' -dicyclohexylcarbodiimide into the O-carboxymethyl chitosan aqueous solution obtained in the step 1 to uniformly stir, adding a proper amount of ginsenoside Rh2 solution obtained in the step 2 to uniformly stir, enabling ginsenoside Rh2 to fully react with O-carboxymethyl chitosan, and dialyzing and freeze-drying after the reaction is finished to obtain the O-carboxymethyl chitosan carrying ginsenoside Rh2, wherein the molecular formula structure is shown as follows:
Figure BDA0004103470630000021
step 4: dissolving the O-carboxymethyl chitosan carrying ginsenoside Rh2 obtained in the step 3 in PBS buffer solution, adding a proper amount of polyoxyethylene polyoxypropylene ether, and uniformly stirring to obtain the temperature/pH response ginsenoside-carrying hydrogel.
Preferably, in step 1, the molar concentration of the O-carboxymethyl chitosan aqueous solution is 0.001-0.01 mmol/ml, the dissolution time is 10-90 min, and the dissolution temperature is 25-30 ℃.
Preferably, in the step 2, the molar concentration of the ginsenoside Rh2 is 0.05-0.3 mmol/ml, the dissolution time is 30-60 min, and the dissolution temperature is 25-30 ℃.
Preferably, in step 3, the molar ratio of 4-dimethylaminopyridine to O-carboxymethyl chitosan is 3 to 10mol% and the molar ratio of N, N' -dicyclohexylcarbodiimide to O-carboxymethyl chitosan is 1 to 5mol%.
Preferably, in step 3, the reaction time is 10 to 48 hours and the reaction temperature is 25 to 35 ℃.
Preferably, in step 3, the dialysis temperature is 25 to 35 ℃, the dialysis time is 24 to 72 hours, the drying temperature is-80 ℃, and the drying time is 24 to 72 hours.
Preferably, in the step 4, the concentration of the O-carboxymethyl chitosan carrying ginsenoside Rh2 is 1-5 w/v%, the mass fraction of the polyoxyethylene polyoxypropylene ether is 20-80 wt%, and the stirring time is 30-60 min.
The invention also provides a temperature/pH response ginsenoside-carrying hydrogel prepared by the method, which can be used for releasing ginsenoside Rh2 by grafting.
The invention also provides an application of the ginsenoside-carrying hydrogel adopting temperature/pH response in preparing anti-inflammatory and analgesic drugs, which can be applied to the field of drug delivery.
Compared with the prior art, the invention has the following beneficial effects:
1. the invention utilizes the ginsenoside crosslinking technology to prepare the ginsenoside-carrying hydrogel with temperature/pH response, and the ginsenoside-carrying hydrogel prepared by the invention has excellent biocompatibility and temperature and pH response performance.
2. The preparation method is simple and flexible, can effectively control the release rate of ginsenoside Rh2, and can be applied to the field of drug delivery.
Drawings
FIG. 1 is a nuclear magnetic resonance diagram of O-carboxymethyl chitosan of ginsenoside Rh2 prepared by the method;
FIG. 2 is a diagram showing temperature sensing at various temperatures of the prepared ginsenoside Rh2 hydrogel according to the present invention, wherein (a) is liquid at 25℃and (b) becomes hydrogel at 37 ℃.
Detailed Description
The following technical solutions in the embodiments of the present invention will be clearly and completely described with reference to the accompanying drawings, so that those skilled in the art can better understand the advantages and features of the present invention, and thus the protection scope of the present invention is more clearly defined. The described embodiments of the present invention are intended to be only a few, but not all embodiments of the present invention, and all other embodiments that may be made by one of ordinary skill in the art without inventive faculty are intended to be within the scope of the present invention.
Example 1:
a preparation method of temperature/pH response ginsenoside-carrying hydrogel comprises the following specific steps:
step 1, dissolving O-carboxymethyl chitosan in deionized water (0.001 mmol/ml), and mechanically stirring at 25 ℃ for 10min to obtain O-carboxymethyl chitosan aqueous solution;
step 2, dissolving ginsenoside Rh2 in methanol (0.05 mmol/ml), and mechanically stirring at 25 ℃ for 30min to obtain a ginsenoside Rh2 solution;
step 3, adding a proper amount of 4-dimethylaminopyridine (3 mol%) and N, N' -dicyclohexylcarbodiimide (1 mol%) into the O-carboxymethyl chitosan water solution, uniformly stirring the mixture, adding the ginsenoside Rh2 solution obtained in the step 2, uniformly stirring the mixture for 10 hours at 25 ℃, enabling the ginsenoside Rh2 to fully react with the O-carboxymethyl chitosan, dialyzing the mixture for 24 hours at 25 ℃ after the reaction is finished, and freeze-drying the mixture at-80 ℃ for 24 hours to obtain the O-carboxymethyl chitosan carrying the ginsenoside Rh 2;
and 4, dissolving the O-carboxymethyl chitosan carrying the ginsenoside Rh2 obtained in the step 3 in PBS buffer solution (1 w/v%), adding a proper amount of polyoxyethylene polyoxypropylene ether (20 wt%), and uniformly stirring for 30min to obtain the temperature/pH response ginsenoside-carrying hydrogel.
Example 2:
a preparation method of temperature/pH response ginsenoside-carrying hydrogel comprises the following specific steps:
step 1, dissolving O-carboxymethyl chitosan in deionized water (0.005 mmol/ml), and mechanically stirring at 25 ℃ for 30min to obtain O-carboxymethyl chitosan aqueous solution;
step 2, dissolving ginsenoside Rh2 in methanol (0.1 mmol/ml), and mechanically stirring at 25 ℃ for 30min to obtain a ginsenoside Rh2 solution;
step 3, adding a proper amount of 4-dimethylaminopyridine (5 mol%) and N, N' -dicyclohexylcarbodiimide (2 mol%) into the O-carboxymethyl chitosan water solution, uniformly stirring the mixture, adding the ginsenoside Rh2 solution obtained in the step 2, uniformly stirring the mixture for 24 hours at 25 ℃, enabling the ginsenoside Rh2 to fully react with the O-carboxymethyl chitosan, dialyzing the mixture for 48 hours at 30 ℃ after the reaction is finished, and freeze-drying the mixture at-80 ℃ for 48 hours to obtain the O-carboxymethyl chitosan carrying the ginsenoside Rh 2;
and 4, dissolving the O-carboxymethyl chitosan carrying ginsenoside Rh2 obtained in the step 3 in PBS buffer solution (2 w/v%), adding a proper amount of polyoxyethylene polyoxypropylene ether (30 wt%), and uniformly stirring for 30min to obtain the temperature/pH response ginsenoside-carrying hydrogel.
Example 3:
a preparation method of temperature/pH response ginsenoside-carrying hydrogel comprises the following specific steps:
step 1, dissolving O-carboxymethyl chitosan in deionized water (0.01 mmol/ml), and mechanically stirring at 25 ℃ for 60min to obtain O-carboxymethyl chitosan aqueous solution;
step 2, dissolving ginsenoside Rh2 in methanol (0.3 mmol/ml), and mechanically stirring at 25 ℃ for 60min to obtain a ginsenoside Rh2 solution;
step 3, adding a proper amount of 4-dimethylaminopyridine (10 mol%) and N, N' -dicyclohexylcarbodiimide (5 mol%) into the O-carboxymethyl chitosan water solution, uniformly stirring the mixture, adding the ginsenoside Rh2 solution obtained in the step 2, uniformly stirring the mixture for 24 hours at 25 ℃, enabling the ginsenoside Rh2 to fully react with the O-carboxymethyl chitosan, dialyzing the mixture for 24 hours at 30 ℃ after the reaction is finished, and freeze-drying the mixture at-80 ℃ for 48 hours to obtain the O-carboxymethyl chitosan carrying the ginsenoside Rh 2;
and 4, dissolving the O-carboxymethyl chitosan carrying the ginsenoside Rh2 obtained in the step 3 in PBS buffer solution (3 w/v%), adding a proper amount of polyoxyethylene polyoxypropylene ether (50 wt%), and uniformly stirring for 60min to obtain the temperature/pH response ginsenoside-carrying hydrogel.
And (3) performance detection:
nuclear magnetic resonance experiments were performed on the ginsenoside Rh 2-carrying O-carboxymethyl chitosan obtained in the above examples, and temperature response and release rate tests were performed on the temperature/pH response ginsenoside-carrying hydrogel, specifically including: testing the phase change of the ginsenoside-carrying hydrogel at different temperatures; the ginsenoside-carrying hydrogel is placed in a dialysis membrane, placed in PBS buffer solutions with different pH values, and shaken in a water bath kettle at 37 ℃, and the release rate of the ginsenoside-carrying hydrogel in different pH environments is tested.
The test result shows that the ginsenoside-carrying hydrogel obtained by the invention has a temperature response effect, is liquid at 25 ℃ (figure 2 (a)) and becomes hydrogel at 37 ℃ (figure 2 (b)); ginsenoside is released more rapidly under acidic conditions than under alkaline conditions.
Table 1 effect of pH on release rate of ginsenoside Rh 2:
Figure BDA0004103470630000051
a temperature/pH response ginsenoside-carrying hydrogel can be applied to the field of drug delivery by grafting and effectively releasing ginsenoside Rh 2.
In summary, the ginsenoside-carrying hydrogel with temperature/pH response is prepared by utilizing the ginsenoside crosslinking technology, and the ginsenoside-carrying hydrogel prepared by the invention has excellent biocompatibility and temperature and pH response performance.
The description and practice of the invention disclosed herein will be readily apparent to those skilled in the art, and may be modified and adapted in several ways without departing from the principles of the invention. Accordingly, modifications or improvements may be made without departing from the spirit of the invention and are also to be considered within the scope of the invention.

Claims (9)

1. A preparation method of a temperature/pH response ginsenoside-carrying hydrogel is characterized by comprising the following specific steps:
step 1: dissolving O-carboxymethyl chitosan in deionized water, and mechanically stirring to obtain O-carboxymethyl chitosan aqueous solution;
step 2: dissolving ginsenoside Rh2 in methanol, and mechanically stirring to obtain ginsenoside Rh2 solution;
step 3: adding a proper amount of 4-dimethylaminopyridine and N, N' -dicyclohexylcarbodiimide into the O-carboxymethyl chitosan aqueous solution obtained in the step 1 to uniformly stir, adding a proper amount of ginsenoside Rh2 solution obtained in the step 2 to uniformly stir, enabling ginsenoside Rh2 to fully react with O-carboxymethyl chitosan, and dialyzing and freeze-drying after the reaction is finished to obtain the O-carboxymethyl chitosan carrying ginsenoside Rh 2;
step 4: dissolving the O-carboxymethyl chitosan carrying ginsenoside Rh2 obtained in the step 3 in PBS buffer solution, adding a proper amount of polyoxyethylene polyoxypropylene ether, and uniformly stirring to obtain the temperature/pH response ginsenoside-carrying hydrogel.
2. The method for preparing a temperature/pH responsive ginsenoside-carrying hydrogel according to claim 1, wherein in step 1, the molar concentration of the O-carboxymethyl chitosan aqueous solution is 0.001-0.01 mmol/ml, the dissolution time is 10-90 min, and the dissolution temperature is 25-30 ℃.
3. The method for preparing a temperature/pH responsive ginsenoside-carrying hydrogel according to claim 1, wherein in step 2, the molar concentration of ginsenoside Rh2 is 0.05-0.3 mmol/ml, the dissolution time is 30-60 min, and the dissolution temperature is 25-30 ℃.
4. The method for preparing a temperature/pH responsive ginsenoside-carrying hydrogel according to claim 1, wherein in step 3, the molar ratio of 4-dimethylaminopyridine to O-carboxymethyl chitosan is 3 to 10mol%, and the molar ratio of N, N' -dicyclohexylcarbodiimide to O-carboxymethyl chitosan is 1 to 5mol%.
5. The method for preparing a temperature/pH responsive ginsenoside-carrying hydrogel according to claim 1, wherein in step 3, the reaction time is 10 to 48 hours and the reaction temperature is 25 to 35 ℃.
6. The method for preparing a temperature/pH responsive ginsenoside-carrying hydrogel according to claim 1, wherein in step 3, the dialysis temperature is 25 to 35 ℃, the dialysis time is 24 to 72 hours, the drying temperature is-80 ℃, and the drying time is 24 to 72 hours.
7. The method for preparing a temperature/pH responsive ginsenoside-carrying hydrogel according to claim 1, wherein in step 4, the concentration of the O-carboxymethyl chitosan carrying ginsenoside Rh2 is 1-5 w/v%, the mass fraction of the polyoxyethylene polyoxypropylene ether is 20-80 wt%, and the stirring time is 30-60 min.
8. A temperature/pH responsive ginsenoside-carrying hydrogel prepared by the method of any one of claims 1-7, characterized in that it is used for the release of ginsenoside Rh2 by grafting.
9. Use of a temperature/pH responsive ginsenoside-carrying hydrogel of claim 8 in the preparation of an anti-inflammatory, analgesic drug.
CN202310185197.XA 2023-03-01 2023-03-01 Preparation method and application of temperature/pH response ginsenoside-carrying hydrogel Pending CN116172944A (en)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101297973A (en) * 2008-05-22 2008-11-05 武汉华纳生物工程有限公司 Highly bioadhesive and thermosensitive hydrogel, and preparation method and application thereof
US20160310516A1 (en) * 2015-03-17 2016-10-27 University-Industry Cooperation Group Of Kyunghee University Conjugate of ginsenoside compound k and glycol chitosan and an anti-tumor use thereof
CN108056928A (en) * 2018-02-06 2018-05-22 三椒口腔健康股份有限公司 A kind of buccal cavity gel of the rare saponin(e containing Radix Notoginseng and preparation method thereof
KR20190014221A (en) * 2017-07-28 2019-02-12 경희대학교 산학협력단 A composition for producing zinc nanocomposites comprising Dendropanax Morbifera extracts and the use thereof
CN113663085A (en) * 2021-08-25 2021-11-19 福州市大福瑞生物科技有限公司 Method for preparing saponin-chitosan derivative based on halogenated alkylene oxide grafting and application thereof

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101297973A (en) * 2008-05-22 2008-11-05 武汉华纳生物工程有限公司 Highly bioadhesive and thermosensitive hydrogel, and preparation method and application thereof
US20160310516A1 (en) * 2015-03-17 2016-10-27 University-Industry Cooperation Group Of Kyunghee University Conjugate of ginsenoside compound k and glycol chitosan and an anti-tumor use thereof
KR20190014221A (en) * 2017-07-28 2019-02-12 경희대학교 산학협력단 A composition for producing zinc nanocomposites comprising Dendropanax Morbifera extracts and the use thereof
CN108056928A (en) * 2018-02-06 2018-05-22 三椒口腔健康股份有限公司 A kind of buccal cavity gel of the rare saponin(e containing Radix Notoginseng and preparation method thereof
CN113663085A (en) * 2021-08-25 2021-11-19 福州市大福瑞生物科技有限公司 Method for preparing saponin-chitosan derivative based on halogenated alkylene oxide grafting and application thereof

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